Sunday, January 27, 2019

organic chemistry - Why does C=O have a larger dipole moment than C-O?


Why does $\ce{C=O}$ have a larger dipole moment than $\ce{C-O}$?


According to me, dipole moment directly depends upon bond length and electronegativity difference. In $\ce{C=O}$ and $\ce{C-O}$, (I guess, please clear if I am wrong) the EN difference is same, and bond length of $\ce{C=O}$ is less than $\ce{C-O}$. So, $\ce{C=O}$ must have less dipole moment than $\ce{C-O}$ but it is not so. Why?



Answer




According to Wikipedia, bond dipole moment depends on:



  1. Distance between atoms and

  2. Overall charge difference, not just electronegativity difference.


Resonance tells us that there is some amount of charge separation in $\ce{C=O}$ bonds because of the $\ce{C+-O-}$ contributor. This difference in charge, in addition to the electronegativity difference, is more significant than the decrease in distance between atoms, hence the larger dipole moment for $\ce{C=O}$.


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